tert-butyl (3S)-3-<(2S,3R)-1-tert-butoxycarbonyl-3-hydroxy-2-pyrrolidinyl>-3-hydroxypropionate | 89985-84-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl (3S)-3-<(2S,3R)-1-tert-butoxycarbonyl-3-hydroxy-2-pyrrolidinyl>-3-hydroxypropionate
• 英文别名: tert-Butyl (3R)-3-Hydroxy-3-<(2R,3S)-3-hydroxy-2-pyrrolidinyl>propionate
• CAS: 89985-84-2
• 化学式: C₁₆H₂₉NO₆
• 分子量: 331.409
• InChiKey: IKQYTQYJICVNEV-MDZLAQPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.45
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  96.3
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (3S)-3-<(2S,3R)-1-tert-butoxycarbonyl-3-hydroxy-2-pyrrolidinyl>-3-hydroxypropionate 、 2,2-二甲氧基丙烷 在 4 A molecular sieve 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以96%的产率得到tert-Butyl <4S-(4α,4aα,7aα)>-5-(tert-Butoxycarbonyl)-hexahydro-2,2-dimethyl-1,3-dioxino<5,4-b>pyrrole-4-acetate
  参考文献：
  名称：

  Total synthesis of (+)-Valyldetoxinine and (−)-detoxin D1

  摘要：

  The detoxin complex, metabolites produced by Streptomyces caespitosus var.detoxicus 7072 GC1, is a selective antagonist of the antibiotic blasticidin S. Two approaches toward the total synthesis of (+)-valyldetoxinine and (-)-detoxin D1 are described These routes involve a 2,3-disubstituted pyrrolidine as a common intermediate and utilize glucose as the chiral precursor

  DOI：

  10.1016/s0040-4020(01)80323-9
• 作为产物：
  描述：

  tert-butyl (3S)-3-<(2S,3R)-1-benzyloxycarbonyl-3-hydroxy-2-pyrrolidinyl>-3-hydroxypropionate 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 5.0h， 生成 tert-butyl (3S)-3-<(2S,3R)-1-tert-butoxycarbonyl-3-hydroxy-2-pyrrolidinyl>-3-hydroxypropionate
  参考文献：
  名称：

  Total synthesis of (+)-Valyldetoxinine and (−)-detoxin D1

  摘要：

  The detoxin complex, metabolites produced by Streptomyces caespitosus var.detoxicus 7072 GC1, is a selective antagonist of the antibiotic blasticidin S. Two approaches toward the total synthesis of (+)-valyldetoxinine and (-)-detoxin D1 are described These routes involve a 2,3-disubstituted pyrrolidine as a common intermediate and utilize glucose as the chiral precursor

  DOI：

  10.1016/s0040-4020(01)80323-9

文献信息

• Asymmetric intramolecular amidation of N-(tert-butoxycarbonyl)-3-hydroxy-4-pentenylamine. A new entry to chiral building blocks for the synthesis of biologically active nitrogen-containing compounds
  作者：Hiroki Takahata、Yasunori Banba、Mayumi Tajima、Takefumi Momose

  DOI：10.1021/jo00001a045

  日期：1991.1

  Sharpless reaction of racemic N-(tert-butoxycarbonyl)-3-hydroxy-4-pentenylamine (1) leads to both an asymmetric kinetic resolution to provide optically active 1, which was subsequently used for intramolecular amidomercuration, and asymmetric epoxidation followed by concomitant cyclization into optically active cis-3-hydroxy-2-(hydroxymethyl)pyrrolidine (3). Optically active 1 and 3 have been expediently used as chiral building blocks in the asymmetric synthesis of several biologically active natural products.